The Florentine sixteenth-century painter, Michele Tosini, advanced the visual ‘afterlife’ of Mary Magdalene through his bust-length portraits of this popular biblical figure. Through the examination of Tosini’s connections to the most influential artists (and their works) and his associations with wealthy Tuscan patrons and intellectual religious communities, we see how this Late Renaissance artist was able to paint the Magdalene as understood by his contemporary culture. The visual sources and precedents of the Tosini Magdalene (Fig. 1) will be discussed in conjunction with the influential biblical narratives, apocryphal legends, and contemporary teachings known to sixteenth-century artists.1 The Magdalene portraits in the beginning of the sixteenth-century were of two types: an aristocratic woman or a voluptuous seductress. The Mary Magdalene paintings by Michele Tosini served as a transition or ‘recasting’ of the biblical figure as it developed within the genre of female portraiture and allowed the post-Trent Baroque portraits of the Magdalene to be sensuous and elegant while regaining her role as penitent and intercessor for the faithful.